I find the type hints harder and slower than java/C/...

try typing a decorator, or anything using file IO

I find it extremely difficult, if not impossible, and I did type theory

(the type checkers being really, really stupid doesn't help either)

So don’t? Just annotate the stuff that’s not annoying. I agree, IO is annoying to type. Decorators are fine, it’s just a function that returns a function. It’s still a win, however much you decide to annotate.